Sodium Carbonate → 3-chloro-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide

HRID 1665016Notes

Reaction equation

HRID 1665016 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[CH3:19][S:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[Cl:18][C:14]1[CH:13]=[C:12]([S:9]([NH:8][CH2:7][C:5]2[S:6][C:2]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH:28]=3)=[CH:3][CH:4]=2)(=[O:11])=[O:10])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 35408893N-(5-bromo-thiophen-2-ylmethyl)-3-chloro-benzenesulfonamide

Product 1

HCID 674421443-chloro-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In analogy to example 1, step 3, N-(5-bromo-thiophen-2-ylmethyl)-3-chloro-benzenesulfonamide was reacted with (3-methylsulfonylphenyl)-boronic acid, Na2CO3 and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct in dioxane/water to give 3-chloro-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide as an off-white solid. MS: 440.3 ([M−H]−)

Sources & evidence

ORD record
ord-b045c42dbcf342d1bdcf0b052062877d
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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